Oxalyl chloride → HCID 178473906, compound

HRID 986251Notes

Reaction equation

HRID 986251 reaction equation
[C:1]([N:4]1[CH2:9][CH2:8][N:7]([CH2:10][CH2:11][N:12]2[C:25]3[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=3)[C:19](=O)[C:18]3[CH:17]=[CH:16][CH:15]=[CH:14][C:13]2=3)[CH2:6][CH2:5]1)(=[O:3])[CH3:2].C(Cl)(=O)C(Cl)=O.Br.[NH:34]([C:36]1[S:37][CH2:38][CH2:39][N:40]=1)[NH2:35].C([O-])(=O)C.[Na+]>C(#N)C.CO>[S:37]1[CH2:38][CH2:39][NH:40][C:36]1=[N:34][N:35]=[C:19]1[C:20]2[CH:21]=[CH:22][CH:23]=[CH:24][C:25]=2[N:12]([CH2:11][CH2:10][N:7]2[CH2:8][CH2:9][N:4]([C:1](=[O:3])[CH3:2])[CH2:5][CH2:6]2)[C:13]2[C:18]1=[CH:17][CH:16]=[CH:15][CH:14]=2

Participants

7

Reactant 4

HCID 65578Oxalyl chlorideHCID 517045Sodium AcetateHCID 27743032-Thiazolidinone, hydrazone, hydrobromideHCID 1401488610-[2-(4-Acetyl-1-piperazinyl)ethyl]-9-acridanone

Product 1

HCID 178473906HCID 178473906, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6342AcetonitrileSolvent

Procedure

A suspension of 3.5 g of 10-[2-(4-acetyl-1-piperazinyl)ethyl]-9-acridanone in 100 ml of acetonitrile is treated with 1.7 ml of oxalyl chloride, suction filtered after 0.5 hour and the suction filter material (9-chloro-10-[2-(4-acetyl-1-piperazinyl)ethyl]acridinium chloride) is washed successively with acetonitrile and ether. A mixture of the substance obtained is heated to boiling under reflux with 2 g of 2-hydrazino-2-thiazoline hydrobromide, 2.5 g of sodium acetate and 100 ml of methanol and evaporated after 15 minutes. The residue is treated with water, made alkaline with sodium carbonate solution and extracted with methylene chloride. The extract is washed with water, dried and evaporated, whereupon the residue is crystallized from methanol. After recrystallization from n-butanol, there is obtained 10-[2-(4-acetyl-1-piperazinyl)ethyl]-9-acridanone (2-thiazolidinylidene)hydrazone of melting point 256°.

Workup

  1. filtrationfiltered after 0.5 hour
  2. filtrationthe suction filter material (9-chloro-10-[2-(4-acetyl-1-piperazinyl)ethyl]acridinium chloride)
  3. washis washed successively with acetonitrile and ether
  4. additionA mixture of the substance
  5. customobtained
  6. temperatureis heated
  7. customevaporated after 15 minutes
  8. additionThe residue is treated with water
  9. extractionextracted with methylene chloride
  10. washThe extract is washed with water
  11. customdried
  12. customevaporated, whereupon the residue
  13. customis crystallized from methanol
  14. customAfter recrystallization from n-butanol

Sources & evidence

ORD record
ord-dfd8561cca064075b95b8676bd60bf3b
Source dataset
uspto-grants-1987_12
Patent number
US04711889

Reaction notes

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